I thought I could quit claim it...but again I'm a newbie to commercial. 

Is it worth claiming this deduction and if so what have others done to maximize the tax benefit?

Otherwise,  the tenant can claim they paid rent but not the late fee, and you cannot penalize them for it. 

Also, because most are inexperienced, they may have unrealistic expectations.

It's those maniacs that buy homes cash via quit claim deed off of craigslist that really get screwed.Make sure your property manager is a licensed real estate brokerage.Understand you can not eliminate all risk, only mitigate it.

Someone who's been there for 10 years will have a better claim to the space than someone 2 months. 

Here is an excerpt from an article on the subject that I believe breaks this down fairly well:Gain, to the extent of the depreciation claimed that exceeds what would have been allowable under straight-line depreciation, will be recaptured as ordinary income, and, thus, taxed at rates as high as 35% in 2003 and later years (ordinary income rates), but the amount of excess depreciation subject to recapture may be less for certain low-income housingGain, to the extent of the depreciation that isn't recaptured as ordinary income, will be taxed at a rate of 25%.The balance of the gain will be taxed at a rate of 15%Example – In January 1986, you paid $1.3 million for an apartment building (not a low-income building), of which $1 million was allocated to the improvements.

If you get the house under contract, send someone to look at it, then realize the repairs are much more hefty than the seller claimed and you can't make a profit, you can go back and renegotiate the price within that inspection period.

Get the owner to sign over a Quit Claim Deed from him to "The Holder of this Deed". 

If he adds me as "additional named insured" on his policy, It sounds like we will both be covered in the event of a claim.